cinnarizine   Click here for help

GtoPdb Ligand ID: 9072

Synonyms: R-1575 | Stugeron®
Approved drug PDB Ligand
cinnarizine is an approved drug (UK (1989))
Compound class: Synthetic organic
Comment: Cinnarizine is used primarily for its anti-histaminic activity, but it also has anti-cholinergic and calcium channel blocking effects, which may account for some of its side-effects.The INN record for this drug specifies cinnarizine clofibrate (PubChem CID 6436096). Cinnarizine is the parent molecule of the fluorine derivative flunarizine. Both of these compounds induce parkinsonism as an adverse effect [2,4], likely due to antagonism of D2 receptors by the parent molecules and/or some of their bioactive metabolites [3].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 6
Topological polar surface area 6.48
Molecular weight 368.23
XLogP 5.3
No. Lipinski's rules broken 1
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Canonical SMILES c1ccc(cc1)C=CCN1CCN(CC1)C(c1ccccc1)c1ccccc1
Isomeric SMILES c1ccc(cc1)/C=C/CN1CCN(CC1)C(c1ccccc1)c1ccccc1
InChI InChI=1S/C26H28N2/c1-4-11-23(12-5-1)13-10-18-27-19-21-28(22-20-27)26(24-14-6-2-7-15-24)25-16-8-3-9-17-25/h1-17,26H,18-22H2/b13-10+
1. Arab SF, Düwel P, Jüngling E, Westhofen M, Lückhoff A. (2004)
Inhibition of voltage-gated calcium currents in type II vestibular hair cells by cinnarizine.
Naunyn Schmiedebergs Arch Pharmacol, 369 (6): 570-5. [PMID:15138660]
2. Capellà D, Laporte JR, Castel JM, Tristán C, Cos A, Morales-Olivas FJ. (1988)
Parkinsonism, tremor, and depression induced by cinnarizine and flunarizine.
BMJ, 297 (6650): 722-3. [PMID:3147743]
3. Kariya S, Isozaki S, Masubuchi Y, Suzuki T, Narimatsu S. (1995)
Possible pharmacokinetic and pharmacodynamic factors affecting parkinsonism inducement by cinnarizine and flunarizine.
Biochem Pharmacol, 50 (10): 1645-50. [PMID:7503767]
4. Teive HA, Troiano AR, Germiniani FM, Werneck LC. (2004)
Flunarizine and cinnarizine-induced parkinsonism: a historical and clinical analysis.
Parkinsonism Relat Disord, 10 (4): 243-5. [PMID:15120099]